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Metallation of heteroaryls and its application to isotopic labelling
Author(s) -
Allen Paul H.,
Coissard Vincent,
Hickey Michael J.,
Hogg Colin,
Kingston Lee P.,
Caffrey Moya,
Wilkinson David J.
Publication year - 2010
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1721
Subject(s) - chemistry , labelling , regioselectivity , deuterium , iodine , metalation , lithium (medication) , halogenation , organic chemistry , radiochemistry , catalysis , medicine , biochemistry , physics , quantum mechanics , endocrinology
The recently published procedure for the metallation of heteroaromatics and their subsequent reaction with iodine has been applied to the synthesis of deuterium‐labelled compounds. The mixed magnesium/lithium base (2) has been prepared and reacted with a range of heteroaromatics. The metallated compounds were iodolyzed with molecular iodine and the resulting iodo compounds were reductively dehalogenated with deuterium gas. This allowed confirmation of the regiochemistry of the metallation and the use of the procedure as a labelling method. Copyright © 2009 John Wiley & Sons, Ltd.